#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:51:47 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179543 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/12/4501222.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4501222
loop_
_publ_author_name
'Zhang, Zhi-Hui'
'Chen, Sheng-Chun'
'He, Ming-Yang'
'Li, Chao'
'Chen, Qun'
'Du, Miao'
_publ_section_title
;
 Fluorine-Induced Chiral Coordination Arrays Containing Helical
 Hydrogen-Bonding Chains of Water or Fluorinated Ligand
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5171
_journal_paper_doi               10.1021/cg200902g
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C24 H20 N4 O9 Zn2'
_chemical_formula_weight         639.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.609(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.294(3)
_cell_length_b                   16.269(4)
_cell_length_c                   11.180(3)
_cell_measurement_reflns_used    749
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.26
_cell_measurement_theta_min      2.54
_cell_volume                     2384.1(10)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL and DIAMOND (Brandenburg, 2005)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL(Scheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1248
_diffrn_reflns_av_sigmaI/netI    0.1324
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10262
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    2.077
_exptl_absorpt_correction_T_max  0.611
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1449
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0453P)²+3.3647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                1380
_reflns_number_total             2745
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200902g_si_002.cif
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4501222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.29362(5) 0.13742(4) 0.18194(6) 0.0255(2) Uani 1 1 d .
C1 C 0.1473(5) 0.2128(4) 0.3451(6) 0.0451(18) Uani 1 1 d .
H1 H 0.1730 0.2637 0.3272 0.054 Uiso 1 1 calc R
C2 C 0.0776(5) 0.2101(4) 0.4266(6) 0.051(2) Uani 1 1 d .
H2 H 0.0585 0.2579 0.4625 0.061 Uiso 1 1 calc R
C3 C 0.0382(5) 0.1353(5) 0.4520(6) 0.0433(17) Uani 1 1 d .
H3 H -0.0095 0.1317 0.5039 0.052 Uiso 1 1 calc R
C4 C 0.0707(5) 0.0653(4) 0.3992(6) 0.0443(19) Uani 1 1 d .
H4 H 0.0466 0.0138 0.4170 0.053 Uiso 1 1 calc R
C5 C 0.1385(4) 0.0728(4) 0.3208(5) 0.0306(15) Uani 1 1 d .
C6 C 0.1793(5) 0.0012(4) 0.2626(5) 0.0333(15) Uani 1 1 d .
H6 H 0.1576 -0.0517 0.2769 0.040 Uiso 1 1 calc R
C7 C 0.2859(5) -0.0608(4) 0.1423(6) 0.0361(16) Uani 1 1 d .
H7A H 0.2796 -0.0551 0.0550 0.043 Uiso 1 1 calc R
H7B H 0.2482 -0.1093 0.1593 0.043 Uiso 1 1 calc R
C8 C 0.3978(4) -0.0699(3) 0.1987(5) 0.0265(14) Uani 1 1 d .
C9 C 0.4271(5) -0.0730(4) 0.3246(5) 0.0301(14) Uani 1 1 d .
H9 H 0.3779 -0.0762 0.3747 0.036 Uiso 1 1 calc R
C10 C 0.4719(5) -0.0713(3) 0.1262(6) 0.0312(15) Uani 1 1 d .
H10 H 0.4528 -0.0711 0.0423 0.037 Uiso 1 1 calc R
C11 C 0.2238(4) 0.2155(3) -0.0423(5) 0.0238(13) Uani 1 1 d .
C12 C 0.5065(4) 0.1332(3) 0.1822(5) 0.0230(12) Uani 1 1 d .
N1 N 0.1779(3) 0.1473(3) 0.2931(4) 0.0299(12) Uani 1 1 d .
N2 N 0.2435(4) 0.0129(3) 0.1938(4) 0.0279(12) Uani 1 1 d .
O1 O 0.2119(3) 0.1469(2) 0.0047(3) 0.0276(9) Uani 1 1 d .
O2 O 0.1975(3) 0.2334(2) -0.1527(3) 0.0289(10) Uani 1 1 d .
O3 O 0.4271(3) 0.1283(2) 0.1046(3) 0.0269(9) Uani 1 1 d .
O4 O 0.5960(3) 0.1383(2) 0.1614(3) 0.0269(9) Uani 1 1 d .
O5 O 0.0000 0.1514(4) 0.7500 0.0487(18) Uani 1 2 d S
H5 H 0.0380 0.1937 0.7601 0.073 Uiso 1 1 d R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O4 Zn1 O1 166.13(14) 2_655 .
O4 Zn1 O3 79.77(14) 2_655 .
O1 Zn1 O3 87.49(14) . .
O4 Zn1 O2 94.18(15) 2_655 7
O1 Zn1 O2 79.40(14) . 7
O3 Zn1 O2 86.24(15) . 7
O4 Zn1 N1 89.13(16) 2_655 .
O1 Zn1 N1 103.54(16) . .
O3 Zn1 N1 168.90(16) . .
O2 Zn1 N1 94.52(17) 7 .
O4 Zn1 N2 97.85(16) 2_655 .
O1 Zn1 N2 90.62(16) . .
O3 Zn1 N2 104.55(17) . .
O2 Zn1 N2 165.06(17) 7 .
N1 Zn1 N2 76.92(19) . .
N1 C1 C2 123.4(6) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C3 C2 C1 118.5(6) . .
C3 C2 H2 120.7 . .
C1 C2 H2 120.7 . .
C2 C3 C4 118.9(6) . .
C2 C3 H3 120.5 . .
C4 C3 H3 120.5 . .
C5 C4 C3 119.2(6) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 N1 122.8(6) . .
C4 C5 C6 122.8(6) . .
N1 C5 C6 114.4(5) . .
N2 C6 C5 119.1(6) . .
N2 C6 H6 120.4 . .
C5 C6 H6 120.4 . .
N2 C7 C8 109.1(5) . .
N2 C7 H7A 109.9 . .
C8 C7 H7A 109.9 . .
N2 C7 H7B 109.9 . .
C8 C7 H7B 109.9 . .
H7A C7 H7B 108.3 . .
C10 C8 C9 119.1(5) . .
C10 C8 C7 120.2(6) . .
C9 C8 C7 120.6(6) . .
C10 C9 C8 119.7(6) 2_655 .
C10 C9 H9 120.1 2_655 .
C8 C9 H9 120.1 . .
C9 C10 C8 121.1(6) 2_655 .
C9 C10 H10 119.5 2_655 .
C8 C10 H10 119.5 . .
O1 C11 O2 125.6(5) . .
O1 C11 C11 117.5(6) . 7
O2 C11 C11 116.9(6) . 7
O3 C12 O4 126.3(5) . .
O3 C12 C12 117.2(6) . 2_655
O4 C12 C12 116.5(6) . 2_655
C1 N1 C5 117.2(5) . .
C1 N1 Zn1 128.7(4) . .
C5 N1 Zn1 113.8(4) . .
C6 N2 C7 117.3(5) . .
C6 N2 Zn1 115.5(4) . .
C7 N2 Zn1 126.7(4) . .
C11 O1 Zn1 112.3(3) . .
C11 O2 Zn1 111.4(3) . 7
C12 O3 Zn1 112.5(3) . .
C12 O4 Zn1 113.6(3) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O4 2.089(4) 2_655
Zn1 O1 2.101(4) .
Zn1 O3 2.105(4) .
Zn1 O2 2.133(4) 7
Zn1 N1 2.139(5) .
Zn1 N2 2.144(5) .
C1 N1 1.312(8) .
C1 C2 1.404(9) .
C1 H1 0.9300 .
C2 C3 1.374(9) .
C2 H2 0.9300 .
C3 C4 1.384(9) .
C3 H3 0.9300 .
C4 C5 1.363(8) .
C4 H4 0.9300 .
C5 N1 1.375(7) .
C5 C6 1.481(8) .
C6 N2 1.255(7) .
C6 H6 0.9300 .
C7 N2 1.482(7) .
C7 C8 1.523(8) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C10 1.377(8) .
C8 C9 1.397(8) .
C9 C10 1.364(8) 2_655
C9 H9 0.9300 .
C10 C9 1.364(8) 2_655
C10 H10 0.9300 .
C11 O1 1.255(6) .
C11 O2 1.259(6) .
C11 C11 1.555(11) 7
C12 O3 1.252(6) .
C12 O4 1.252(6) .
C12 C12 1.554(10) 2_655
O2 Zn1 2.133(4) 7
O4 Zn1 2.089(4) 2_655
O5 H5 0.8501 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O2 0.8500 2.2700 2.984(5) 141.00 1_556 yes
C10 H10 O4 0.9300 2.5100 3.372(7) 154.00 5_655 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 -1.0(11) . .
C1 C2 C3 C4 1.8(10) . .
C2 C3 C4 C5 -1.9(10) . .
C3 C4 C5 N1 1.2(10) . .
C3 C4 C5 C6 178.5(6) . .
C4 C5 C6 N2 -178.2(6) . .
N1 C5 C6 N2 -0.7(8) . .
N2 C7 C8 C10 -122.1(6) . .
N2 C7 C8 C9 54.8(7) . .
C10 C8 C9 C10 4.7(8) . 2_655
C7 C8 C9 C10 -172.2(5) . 2_655
C9 C8 C10 C9 -2.1(8) . 2_655
C7 C8 C10 C9 174.8(5) . 2_655
C2 C1 N1 C5 0.2(10) . .
C2 C1 N1 Zn1 -173.2(5) . .
C4 C5 N1 C1 -0.3(9) . .
C6 C5 N1 C1 -177.8(5) . .
C4 C5 N1 Zn1 174.0(5) . .
C6 C5 N1 Zn1 -3.4(6) . .
O4 Zn1 N1 C1 79.6(5) 2_655 .
O1 Zn1 N1 C1 -94.7(5) . .
O3 Zn1 N1 C1 78.9(11) . .
O2 Zn1 N1 C1 -14.6(6) 7 .
N2 Zn1 N1 C1 177.8(6) . .
O4 Zn1 N1 C5 -94.0(4) 2_655 .
O1 Zn1 N1 C5 91.7(4) . .
O3 Zn1 N1 C5 -94.6(10) . .
O2 Zn1 N1 C5 171.9(4) 7 .
N2 Zn1 N1 C5 4.3(4) . .
C5 C6 N2 C7 177.1(5) . .
C5 C6 N2 Zn1 4.6(7) . .
C8 C7 N2 C6 -110.8(6) . .
C8 C7 N2 Zn1 60.8(6) . .
O4 Zn1 N2 C6 82.4(4) 2_655 .
O1 Zn1 N2 C6 -108.6(4) . .
O3 Zn1 N2 C6 163.8(4) . .
O2 Zn1 N2 C6 -60.9(9) 7 .
N1 Zn1 N2 C6 -4.8(4) . .
O4 Zn1 N2 C7 -89.3(4) 2_655 .
O1 Zn1 N2 C7 79.7(4) . .
O3 Zn1 N2 C7 -7.9(5) . .
O2 Zn1 N2 C7 127.4(6) 7 .
N1 Zn1 N2 C7 -176.5(5) . .
O2 C11 O1 Zn1 168.1(5) . .
C11 C11 O1 Zn1 -11.5(7) 7 .
O4 Zn1 O1 C11 -50.0(8) 2_655 .
O3 Zn1 O1 C11 -73.2(4) . .
O2 Zn1 O1 C11 13.4(4) 7 .
N1 Zn1 O1 C11 105.5(4) . .
N2 Zn1 O1 C11 -177.8(4) . .
O1 C11 O2 Zn1 168.7(4) . 7
C11 C11 O2 Zn1 -11.8(7) 7 7
O4 C12 O3 Zn1 -172.0(5) . .
C12 C12 O3 Zn1 7.7(4) 2_655 .
O4 Zn1 O3 C12 -4.5(4) 2_655 .
O1 Zn1 O3 C12 170.0(4) . .
O2 Zn1 O3 C12 90.5(4) 7 .
N1 Zn1 O3 C12 -3.8(11) . .
N2 Zn1 O3 C12 -100.0(4) . .
O3 C12 O4 Zn1 -176.2(5) . 2_655
C12 C12 O4 Zn1 4.0(4) 2_655 2_655
